Tetrahydrofuran → (E)-(4-methoxyphenyl)(4-styrylquinolin-6-yl)methanone

Participants

Reaction Conditions

Reaction Steps

To a solution of (E)-N-methoxy-N-methyl-4-styrylquinoline-6-carboxamide (150 mg, 0.47 mmol) in anhydrous THF (2 mL) was dropwise added dropwise (4-chlorophenyl)magnesium bromide (0.5 M, 1.23 mL, 0.61 mmol) at 0° C. under N2 and the resulting reaction mixture was stirred at 0° C. for 3 hr. The reaction was diluted with CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2 and the combined organics were concentrated and purified by chromatography (15-20% EtOAc/hexanes) to yield (E)-(4-methoxyphenyl)(4-styrylquinolin-6-yl)methanone. (ES, m/z) 366.0 [M+H]+

Provenance & Evidence